tipranavir

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 470610685

| image = File:Tipranavir structure 2.svg

| image_class = skin-invert-image

| width = 275

| alt =

| pronounce = {{IPAc-en|t|ɪ|p|ˈ|r|æ|n|ə|v|ɪər}}
{{respell|tip|RAN|ə|veer}}

| tradename = Aptivus

| Drugs.com = {{drugs.com|monograph|tipranavir}}

| MedlinePlus = a606009

| licence_EU = yes

| DailyMedID = Tipranavir

| licence_US = Tipranavir

| pregnancy_AU = B3

| pregnancy_US = C

| routes_of_administration = By mouth (soft capsules)

| ATC_prefix = J05

| ATC_suffix = AE09

| ATC_supplemental =

| legal_UK = POM

| legal_US = Rx-only

| legal_US_comment =

| legal_EU = Rx-only

| legal_status =

| bioavailability =

| protein_bound = 99.9%

| metabolism = Liver

| elimination_half-life = 4.8–6 hours

| excretion = Feces (82.3%), urine (4.4%)

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 174484-41-4

| PubChem = 54682461

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00932

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10482313

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ZZT404XD09

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 183041

| NIAID_ChemDB = 032941

| PDB_ligand = TPV

| IUPAC_name = N-{3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-(2-phenylethyl)-2-propyl-3,4-dihydro-2H-pyran-5-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide

| C=31 | H=33 | F=3 | N=2 | O=5 | S=1

| smiles = CCC[C@]1(CC(/O)=C(\C(=O)O1)[C@H](CC)c3cccc(NS(=O)(=O)c2ccc(cn2)C(F)(F)F)c3)CCc4ccccc4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SUJUHGSWHZTSEU-FYBSXPHGSA-N

}}

Tipranavir (TPV), or tipranavir disodium, is a nonpeptidic protease inhibitor (PI) manufactured by Boehringer Ingelheim under the trade name Aptivus {{IPAc-en|ˈ|æ|p|t|ᵻ|v|ə|s}} {{respell|AP|tiv-əs}}. It is administered with ritonavir in combination therapy to treat HIV infection.{{cn|date=November 2022}}

Tipranavir has the ability to inhibit the replication of viruses that are resistant to other protease inhibitors and is recommended for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple mutations.{{cite journal | vauthors = Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley MG | title = Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir | journal = Antiviral Research | volume = 68 | issue = 1 | pages = 27–35 | date = October 2005 | pmid = 16122817 | doi = 10.1016/j.antiviral.2005.07.003 }} Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008.{{cite press release | title = New Aptivus (tipranavir) Oral Solution Approved for Treatment-Experienced Pediatric and Adolescent HIV Patients | publisher = Boehringer Ingelheim | date = 2008-06-24 | url = http://us.boehringer-ingelheim.com/newsroom/2008/06-25-08_aptivus_pediatric.html | access-date = 2008-09-02}}

Tipranavir should only be taken in combination with ritonavir and other antiretroviral drugs, and is not approved for treatment-naïve patients.{{cite web | title=Aptivus- tipranavir capsule, liquid filled Aptivus- tipranavir solution | website=DailyMed | date=26 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=08982e49-d2eb-4b25-b01a-1be52fd669ef | access-date=2 December 2020}} Like lopinavir and atazanavir, it is very potent and is effective in salvage therapy for patients with drug resistance. However, side effects of tipranavir may be more severe than those of other antiretrovirals. Some side effects include intracranial hemorrhage, hepatitis, hepatic decompensation, hyperglycemia and diabetes mellitus. The drug has also been shown to cause increases in total cholesterol and triglycerides.

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.